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access2-(7-Methoxy-1-naphthyl)acetonitrile
aCollege of Food Science and Light Industry, Nanjing University of Technology, Xinmofan Road No.5 Nanjing, Nanjing 210009, People's Republic of China, and bCollege of Science, Nanjing University of Technology, Xinmofan Road No.5 Nanjing, Nanjing 210009, People's Republic of China
*Correspondence e-mail: wanghaibo@njut.edu.cn
The molecule of the title compound, C13H11NO, is almost planar (r.m.s. deviation = 0.013 Å), apart from the cyanide group, for which the C and N atoms deviate from the mean plane of the other atoms by 0.341 (3) and 0.571 (4) Å, respectively. In the crystal, weak aromatic π–π stacking [centroid–centroid distance = 3.758 (3) Å] may help to stabilize the structure.
Related literature
For background to the use of naphthylethyl acetonitrile as an intermediate for the synthesisis of N-naphthylethyl amide derivatives, see: Depreux & Lesieur (1994![[Depreux, P. & Lesieur, D. (1994). J. Med. Chem. 37, 3231-3239.]](../../../../../../logos/arrows/e_arr.gif "Depreux, P. & Lesieur, D. (1994). J. Med. Chem. 37, 3231-3239.")
). For further synthetic details, see: Yous & Andrieux (1992).
![[Scheme 1]](hb5505scheme1.gif)
Experimental
Crystal data
|
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON.
Supporting information
contains datablocks global, I. DOI: 10.1107/S1600536810024372/hb5505sup1.cif
Structure factors: contains datablock I. DOI: 10.1107/S1600536810024372/hb5505Isup2.hkl
(7-Methoxy-1-naphthyl)acetic acid was reacted with thionyl chloride in CHCl3, and the crude acid chloride was treated with aqueous ammonia to produce (7-Methoxy-1-naphthyl)acetamide. Dehydration of this amide with trifluoroacetic anhydride in THF at 273 K gave the title compound (Yous & Andrieux, 1992). Crystals suitable for X-ray analysis were obtained by slow evaporation of a methanol solution (yield; 66%, m.p. 353 K).
H atoms were positioned geometrically, with C—H = 0.93 Å for aromatic H and C—H = 0.96 and 0.97 Å for methyl and methylene H, respectively, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C,O), where x = 1.5 for OH H and x = 1.2 for all other H atoms.
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).
![[Figure 1]](./hb5505fig1thm.gif) | Fig. 1. View of the title compound with displacement ellipsoids for non-H atoms drawn at the 50% probability level. |
![[Figure 2]](./hb5505fig2thm.gif) | Fig. 2. A packing diagram of title molecule. |
| C13H11NO | F(000) = 416 |
| Mr = 197.23 | Dx = 1.254 Mg m−3 |
| Monoclinic, P21/n | Melting point: 353 K |
| Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
| a = 7.5110 (15) Å | Cell parameters from 25 reflections |
| b = 9.6170 (19) Å | θ = 9–13° |
| c = 14.731 (3) Å | µ = 0.08 mm−1 |
| β = 101.03 (3)° | T = 293 K |
| V = 1044.4 (4) Å3 | Block, colorless |
| Z = 4 | 0.30 × 0.20 × 0.10 mm |
| Enraf–Nonius CAD-4 diffractometer | 1045 reflections with I > 2σ(I) |
| Radiation source: fine-focus sealed tube | Rint = 0.011 |
| Graphite monochromator | θmax = 25.3°, θmin = 2.5° |
| ω/2θ scans | h = −9→8 |
| Absorption correction: ψ scan (North et al., 1968) | k = −11→0 |
| Tmin = 0.976, Tmax = 0.992 | l = 0→17 |
| 1971 measured reflections | 3 standard reflections every 200 reflections |
| 1897 independent reflections | intensity decay: 1% |
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.059 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.163 | H-atom parameters constrained |
| S = 1.00 | w = 1/[σ2(Fo2) + (0.069P)2] where P = (Fo2 + 2Fc2)/3 |
| 1897 reflections | (Δ/σ)max < 0.001 |
| 136 parameters | Δρmax = 0.14 e Å−3 |
| 0 restraints | Δρmin = −0.14 e Å−3 |
| C13H11NO | V = 1044.4 (4) Å3 |
| Mr = 197.23 | Z = 4 |
| Monoclinic, P21/n | Mo Kα radiation |
| a = 7.5110 (15) Å | µ = 0.08 mm−1 |
| b = 9.6170 (19) Å | T = 293 K |
| c = 14.731 (3) Å | 0.30 × 0.20 × 0.10 mm |
| β = 101.03 (3)° |
| Enraf–Nonius CAD-4 diffractometer | 1045 reflections with I > 2σ(I) |
| Absorption correction: ψ scan (North et al., 1968) | Rint = 0.011 |
| Tmin = 0.976, Tmax = 0.992 | 3 standard reflections every 200 reflections |
| 1971 measured reflections | intensity decay: 1% |
| 1897 independent reflections |
| R[F2 > 2σ(F2)] = 0.059 | 0 restraints |
| wR(F2) = 0.163 | H-atom parameters constrained |
| S = 1.00 | Δρmax = 0.14 e Å−3 |
| 1897 reflections | Δρmin = −0.14 e Å−3 |
| 136 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
| x | y | z | Uiso*/Ueq | ||
| O | 0.8616 (3) | −0.2547 (2) | 0.13823 (13) | 0.0718 (6) | |
| N | 0.7349 (5) | 0.1342 (3) | −0.3297 (2) | 0.1076 (12) | |
| C1 | 0.7327 (4) | 0.0786 (3) | −0.2623 (2) | 0.0691 (9) | |
| C2 | 0.7316 (4) | 0.0085 (3) | −0.17484 (17) | 0.0565 (7) | |
| H2A | 0.8471 | −0.0380 | −0.1550 | 0.068* | |
| H2B | 0.6376 | −0.0620 | −0.1842 | 0.068* | |
| C3 | 0.6992 (3) | 0.1069 (3) | −0.09873 (18) | 0.0484 (7) | |
| C4 | 0.6435 (4) | 0.2412 (3) | −0.1174 (2) | 0.0622 (8) | |
| H4A | 0.6228 | 0.2727 | −0.1782 | 0.075* | |
| C5 | 0.6171 (4) | 0.3319 (3) | −0.0472 (3) | 0.0716 (9) | |
| H5A | 0.5794 | 0.4227 | −0.0613 | 0.086* | |
| C6 | 0.6466 (4) | 0.2874 (3) | 0.0411 (2) | 0.0685 (9) | |
| H6A | 0.6293 | 0.3486 | 0.0876 | 0.082* | |
| C7 | 0.7028 (4) | 0.1504 (3) | 0.06461 (19) | 0.0552 (8) | |
| C8 | 0.7346 (4) | 0.1027 (3) | 0.1570 (2) | 0.0675 (9) | |
| H8A | 0.7200 | 0.1635 | 0.2042 | 0.081* | |
| C9 | 0.7857 (4) | −0.0299 (4) | 0.1779 (2) | 0.0685 (9) | |
| H9A | 0.8060 | −0.0596 | 0.2391 | 0.082* | |
| C10 | 0.8086 (4) | −0.1236 (3) | 0.10760 (19) | 0.0564 (7) | |
| C11 | 0.7816 (3) | −0.0820 (3) | 0.01827 (18) | 0.0495 (7) | |
| H11A | 0.7979 | −0.1448 | −0.0275 | 0.059* | |
| C12 | 0.7285 (3) | 0.0571 (3) | −0.00618 (18) | 0.0471 (7) | |
| C13 | 0.8857 (4) | −0.3548 (3) | 0.0708 (2) | 0.0723 (9) | |
| H13A | 0.9233 | −0.4415 | 0.1007 | 0.108* | |
| H13B | 0.9768 | −0.3229 | 0.0380 | 0.108* | |
| H13C | 0.7733 | −0.3677 | 0.0280 | 0.108* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O | 0.0897 (16) | 0.0689 (14) | 0.0570 (12) | 0.0037 (12) | 0.0148 (11) | 0.0088 (11) |
| N | 0.177 (4) | 0.085 (2) | 0.062 (2) | −0.005 (2) | 0.024 (2) | 0.0025 (17) |
| C1 | 0.092 (2) | 0.064 (2) | 0.0507 (18) | −0.0084 (18) | 0.0111 (16) | −0.0041 (16) |
| C2 | 0.0636 (19) | 0.0525 (17) | 0.0549 (17) | −0.0034 (14) | 0.0150 (14) | −0.0016 (14) |
| C3 | 0.0441 (15) | 0.0478 (16) | 0.0553 (17) | −0.0072 (13) | 0.0142 (13) | −0.0041 (13) |
| C4 | 0.065 (2) | 0.0532 (18) | 0.070 (2) | −0.0012 (15) | 0.0164 (15) | 0.0030 (16) |
| C5 | 0.074 (2) | 0.0490 (18) | 0.097 (3) | 0.0035 (16) | 0.0285 (19) | −0.0043 (18) |
| C6 | 0.073 (2) | 0.057 (2) | 0.084 (2) | −0.0069 (16) | 0.0352 (18) | −0.0222 (17) |
| C7 | 0.0506 (17) | 0.0552 (19) | 0.0636 (19) | −0.0093 (14) | 0.0210 (14) | −0.0135 (15) |
| C8 | 0.074 (2) | 0.073 (2) | 0.062 (2) | −0.0102 (18) | 0.0293 (16) | −0.0217 (17) |
| C9 | 0.078 (2) | 0.082 (2) | 0.0499 (17) | −0.0113 (19) | 0.0234 (16) | −0.0027 (17) |
| C10 | 0.0572 (18) | 0.0583 (18) | 0.0552 (18) | −0.0043 (14) | 0.0141 (14) | 0.0006 (15) |
| C11 | 0.0491 (16) | 0.0508 (17) | 0.0519 (17) | −0.0058 (13) | 0.0182 (13) | −0.0061 (13) |
| C12 | 0.0384 (15) | 0.0485 (16) | 0.0565 (17) | −0.0098 (12) | 0.0142 (12) | −0.0069 (13) |
| C13 | 0.078 (2) | 0.0579 (19) | 0.079 (2) | 0.0039 (16) | 0.0087 (18) | 0.0028 (17) |
| O—C10 | 1.372 (3) | C6—H6A | 0.9300 |
| O—C13 | 1.419 (3) | C7—C8 | 1.413 (4) |
| N—C1 | 1.130 (4) | C7—C12 | 1.417 (3) |
| C1—C2 | 1.456 (4) | C8—C9 | 1.350 (4) |
| C2—C3 | 1.522 (3) | C8—H8A | 0.9300 |
| C2—H2A | 0.9700 | C9—C10 | 1.407 (4) |
| C2—H2B | 0.9700 | C9—H9A | 0.9300 |
| C3—C4 | 1.369 (4) | C10—C11 | 1.353 (4) |
| C3—C12 | 1.422 (3) | C11—C12 | 1.422 (4) |
| C4—C5 | 1.396 (4) | C11—H11A | 0.9300 |
| C4—H4A | 0.9300 | C13—H13A | 0.9600 |
| C5—C6 | 1.347 (4) | C13—H13B | 0.9600 |
| C5—H5A | 0.9300 | C13—H13C | 0.9600 |
| C6—C7 | 1.406 (4) | ||
| C10—O—C13 | 117.4 (2) | C8—C7—C12 | 118.8 (3) |
| N—C1—C2 | 179.1 (4) | C9—C8—C7 | 120.9 (3) |
| C1—C2—C3 | 113.2 (2) | C9—C8—H8A | 119.5 |
| C1—C2—H2A | 108.9 | C7—C8—H8A | 119.5 |
| C3—C2—H2A | 108.9 | C8—C9—C10 | 120.4 (3) |
| C1—C2—H2B | 108.9 | C8—C9—H9A | 119.8 |
| C3—C2—H2B | 108.9 | C10—C9—H9A | 119.8 |
| H2A—C2—H2B | 107.8 | C11—C10—O | 124.9 (3) |
| C4—C3—C12 | 119.7 (3) | C11—C10—C9 | 120.6 (3) |
| C4—C3—C2 | 121.6 (3) | O—C10—C9 | 114.5 (3) |
| C12—C3—C2 | 118.7 (2) | C10—C11—C12 | 120.5 (3) |
| C3—C4—C5 | 121.5 (3) | C10—C11—H11A | 119.8 |
| C3—C4—H4A | 119.2 | C12—C11—H11A | 119.8 |
| C5—C4—H4A | 119.2 | C7—C12—C3 | 118.3 (3) |
| C6—C5—C4 | 119.8 (3) | C7—C12—C11 | 118.7 (2) |
| C6—C5—H5A | 120.1 | C3—C12—C11 | 123.0 (2) |
| C4—C5—H5A | 120.1 | O—C13—H13A | 109.5 |
| C5—C6—C7 | 121.4 (3) | O—C13—H13B | 109.5 |
| C5—C6—H6A | 119.3 | H13A—C13—H13B | 109.5 |
| C7—C6—H6A | 119.3 | O—C13—H13C | 109.5 |
| C6—C7—C8 | 121.9 (3) | H13A—C13—H13C | 109.5 |
| C6—C7—C12 | 119.3 (3) | H13B—C13—H13C | 109.5 |
Experimental details
| Crystal data | |
| Chemical formula | C13H11NO |
| Mr | 197.23 |
| Crystal system, space group | Monoclinic, P21/n |
| Temperature (K) | 293 |
| a, b, c (Å) | 7.5110 (15), 9.6170 (19), 14.731 (3) |
| β (°) | 101.03 (3) |
| V (Å3) | 1044.4 (4) |
| Z | 4 |
| Radiation type | Mo Kα |
| µ (mm−1) | 0.08 |
| Crystal size (mm) | 0.30 × 0.20 × 0.10 |
| Data collection | |
| Diffractometer | Enraf–Nonius CAD-4 diffractometer |
| Absorption correction | ψ scan (North et al., 1968) |
| Tmin, Tmax | 0.976, 0.992 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 1971, 1897, 1045 |
| Rint | 0.011 |
| (sin θ/λ)max (Å−1) | 0.601 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.059, 0.163, 1.00 |
| No. of reflections | 1897 |
| No. of parameters | 136 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 0.14, −0.14 |
Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).
Acknowledgements
The authors thank the Center of Testing and Analysis of Nanjing University for support.
References
Depreux, P. & Lesieur, D. (1994). J. Med. Chem. 37, 3231–3239. CrossRef CAS PubMed Web of Science Google Scholar
Enraf–Nonius (1994). CAD-4 EXPRESS. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yous, S. & Andrieux, J. (1992). J. Med. Chem. 35, 1484–1486. CrossRef PubMed CAS Web of Science Google Scholar
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| CRYSTALLOGRAPHIC COMMUNICATIONS |
Naphthylethyl acetonitrile is an important pharmaceutical intermediate for synthesizing N-naphthylethyl amide derivatives which was evaluated as melatonin receptor ligands (Depreux & Lesieur, 1994). We report herein the crystal structure of the title compound, (I).
In the molecule of the title compound (Fig 1), the bond lengths and angles are within normal ranges. Rings A (C3—C7/C12), B (C8—C12)are, of course, planar, and they are oriented at dihedral angle A/B= 1.10 (3) °. So, they are nearly coplanar. No classical hydrogen bond was found in the molecule. The π–π contacts between the naphthalene rings, Cg1—Cg2i [symmetry codes: -x,1 - y,1 - z, where Cg1 and Cg2 are centroids of the rings A (C3—C7/C10/C12), and B (C8—C12), respectively] may further stabilize the structure, with centroid-centroid distances of 3.758 (3) Å.